Sodium Hydroxide → 2-Amino-4-fluorophenol

HRID 323110

反応式

HRID 323110 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-])=O)[CH:3]=1.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[NH2:9][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[CH:6][C:5]=1[OH:8]

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 1362364-Fluoro-2-nitrophenol

生成物 1

HCID 27359172-Amino-4-fluorophenol収率 105.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

A mixture of 4-fluoro-2-nitrophenol(1 g, 4.64 mmol) and tin (II) chloride (5.4 g, 24.2 mmol) in ethanol(50 mL) was heated at 80° C. under argon. After 2 hours, the starting material had disappeared and the solution was allowed to cool down and then poured into ice. The pH is made slightly basic (pH7-8), by addition of solid NaOH, before being extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4% MeOH/CH2Cl2) gave the desired product(622 mg, 85%). 1H NMR (CD3OD): d 6.51 (dd, 1H), 6.32 (dd, 1H), 6.17 (ddd, 1H).

後処理

  1. temperatureto cool down
  2. additionpoured into ice
  3. extractionbefore being extracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was evaporated

出典と根拠

ORDレコード
ord-718e4150d08e4498bb4f559398606039
出典データセット
uspto-grants-2001_04
特許番号
US06211373B1

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